Controllable Emission <italic style="font-style: italic">via</italic> Tuning the Size of Fluorescent Nano-probes Formed by Polymeric Amphiphiles

Xiao-Cheng Wang; Shi-Xin Zhou; Lan Ding; Yu-Han Zhao; Shen-Xi Min; Bin Dong; Bo Song

doi:10.1007/s10118-019-2256-6

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Controllable Emission via Tuning the Size of Fluorescent Nano-probes Formed by Polymeric Amphiphiles

ARTICLE | Updated：2021-02-18

- Controllable Emission via Tuning the Size of Fluorescent Nano-probes Formed by Polymeric Amphiphiles
- Chinese Journal of Polymer Science Vol. 37, Issue 8, Pages: 767-773(2019)
- Affiliations：
  
  a.College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, China
  b.Department of Cell Biology and Stem Cell Research Center, School of Basic Medical Sciences, Peking University Health Science Center, Beijing 100191, China
  c.Institute of Functional Nano & Soft Materials (FUNSOM) & Collaborative Innovation Center for Suzhou Nano Science and Technology, Jiangsu Key Laboratory for Carbon-Based Functional Materials & Devices, Soochow University, Suzhou 215123, China
- Author bio：
  
  songbo@suda.edu.cn
- Funds：
- DOI：10.1007/s10118-019-2256-6
  CLC：
- Received：28 January 2019，
  
  Revised：2019-1-1，
  
  Accepted：18 March 2019，
  
  Online First：24 April 2019，
  
  Published：2019-08
- Accepted：
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Citation: Wang, X. C.; Zhou, S. X.; Ding, L.; Zhao, Y. H.; Min, S. X.; Dong, B.; Song, B. Controllable emission via tuning the size of fluorescent nano-probes formed by polymeric amphiphiles. Chinese J. Polym. Sci. 2019, 37, 767–773

Xiao-Cheng Wang, Shi-Xin Zhou, Lan Ding, et al. Controllable Emission via Tuning the Size of Fluorescent Nano-probes Formed by Polymeric Amphiphiles[J]. Chinese Journal of Polymer Science, 2019, 37(8): 767-773. DOI: 10.1007/s10118-019-2256-6.
Citation: Wang, X. C.; Zhou, S. X.; Ding, L.; Zhao, Y. H.; Min, S. X.; Dong, B.; Song, B. Controllable emission via tuning the size of fluorescent nano-probes formed by polymeric amphiphiles. Chinese J. Polym. Sci. 2019, 37, 767–773 DOI： 10.1007/s10118-019-2256-6.

Xiao-Cheng Wang, Shi-Xin Zhou, Lan Ding, et al. Controllable Emission via Tuning the Size of Fluorescent Nano-probes Formed by Polymeric Amphiphiles[J]. Chinese Journal of Polymer Science, 2019, 37(8): 767-773. DOI: 10.1007/s10118-019-2256-6. DOI：

摘要

Abstract

Incorporating fluorophores into polymeric nanoparticles has been testified as a feasible way to improve the emitting property and bio-compatibility of nano-emitters

which can be applied as fluorescent probes in labeling cells for imaging. Plenty of efforts have been made on the above direction. However

the size effect of nano-emitters has not been addressed yet mainly given the difficulties in controlling morphology and size of the assemblies. In our preceding study

we employed post-polymerization modification method for preparing amphiphilic copolymers

and obtained core-shell (the hydrophobic fluorophores are wrapped inside the nanoparticle to form the core) assemblies in aqueous solution. By this method

we are able to regulate the ratio of the hydrophilic/hydrophobic moieties

and thus alternate the size of the assemblies in a rather simple way. In this study

we synthesized a series of random copolymers by changing the ratio of poly(ethylene glycol) to tetraphenylethylene groups. Notably

the number of repeating units of the polymer was controlled constant for all the copolymers. The self-assembly of these copolymers resulted in different sizes of nanoparticles

and the size decreased with the decreasing fraction of poly(ethylene glycol). Interestingly

the emission of the nanoparticles showed size dependence

and smaller diameter corresponded to stronger emission. Being cultured with HeLa cells

either the large (diameter of ~300 nm) or the small (diameter of ~180 nm) nano-emitters allowed for very high cell viabilities up to 25 μg·mL

−1

. Both of them can be applied in cell imaging and provide high contrast fluorescent images.

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Jin, W. J.; Costa-Fernández, J. M.; Pereiro, R.; Sanz-Medel, A . Surface-modified CdSe quantum dots as luminescent probes for cyanide determination . Anal. Chim. Acta , 2004 . 522 1 - 8 . DOI: 10.1016/j.aca.2004.06.057 http://doi.org/10.1016/j.aca.2004.06.057 .

Gao, X.; Yang, L.; Petros, J. A.; Marshall, F. F.; Simons, J. W.; Nie, S . In vivo molecular and cellular imaging with quantum dots . Curr. Opin. Biotechnol. , 2005 . 16 63 - 72 . DOI: 10.1016/j.copbio.2004.11.003 http://doi.org/10.1016/j.copbio.2004.11.003 .

Zrazhevskiy, P.; Sena, M.; Gao, X . Designing multifunctional quantum dots for bioimaging, detection, and drug delivery . Chem. Soc. Rev. , 2010 . 39 4326 - 4354 . DOI: 10.1039/b915139g http://doi.org/10.1039/b915139g .

Dubertret, B.; Skourides, P.; Norris, D. J.; Noireaux, V.; Brivanlou, A. H.; Libchaber, A . In vivo imaging of quantum dots encapsulated in phospholipid micelles . Science , 2002 . 298 1759 DOI: 10.1126/science.1077194 http://doi.org/10.1126/science.1077194 .

Fernández-Suárez, M.; Ting, A. Y . Fluorescent probes for super-resolution imaging in living cells . Nat. Rev. Mol. Cell Biol. , 2008 . 9 929 - 943 . DOI: 10.1038/nrm2531 http://doi.org/10.1038/nrm2531 .

Zhang, J.; Campbell, R. E.; Ting, A. Y.; Tsien, R. Y . Creating new fluorescent probes for cell biology . Nat. Rev. Mol. Cell Biol. , 2002 . 3 906 - 918 . DOI: 10.1038/nrm976 http://doi.org/10.1038/nrm976 .

Iino, R.; Koyama, I.; Kusumi, A . Single molecule imaging of green fluorescent proteins in living cells: E-cadherin forms oligomers on the free cell surface . Biophys. J. , 2001 . 80 2667 - 2677 . DOI: 10.1016/S0006-3495(01)76236-4 http://doi.org/10.1016/S0006-3495(01)76236-4 .

Nagai, T.; Ibata, K.; Park, E. S.; Kubota, M.; Mikoshiba, K.; Miyawaki, A . A variant of yellow fluorescent protein with fast and efficient maturation for cell-biological applications . Nat. Biotechnol. , 2002 . 20 87 - 90 . DOI: 10.1038/nbt0102-87 http://doi.org/10.1038/nbt0102-87 .

Yang, Z.; Cao, J.; He, Y.; Yang, J. H.; Kim, T.; Peng, X.; Kim, J. S . Macro-/micro-environment-sensitive chemosensing and biological imaging . Chem. Soc. Rev. , 2014 . 43 4563 - 4601 . DOI: 10.1039/C4CS00051J http://doi.org/10.1039/C4CS00051J .

Wu, C.; Hansen, S. J.; Hou, Q.; Yu, J.; Zeigler, M.; Jin, Y.; Burnham, D. R.; McNeill, J. D.; Olson, J. M.; Chiu, D. T . Design of highly emissive polymer dot bioconjugates for in vivo tumor targeting . Angew. Chem. Int. Ed. , 2011 . 123 3492 - 3496 . DOI: 10.1002/ange.201007461 http://doi.org/10.1002/ange.201007461 .

Tao, Z.; Hong, G.; Shinji, C.; Chen, C.; Diao, S.; Antaris, A. L.; Zhang, B.; Zou, Y.; Dai, H . Biological imaging using nanoparticles of small organic molecules with fluorescence emission at wavelengths longer than 1000 nm . Angew. Chem. Int. Ed. , 2013 . 125 13240 - 13244 . DOI: 10.1002/ange.201307346 http://doi.org/10.1002/ange.201307346 .

Ding, D.; Goh, C. C.; Feng, G.; Zhao, Z.; Liu, J.; Liu, R.; Tomczak, N.; Geng, J.; Tang, B. Z.; Ng, L. G., Liu, B . Ultrabright organic dots with aggregation-induced emission characteristics for real-time two-photon intravital vasculature imaging . Adv. Mater. , 2013 . 25 6083 - 6088 . DOI: 10.1002/adma.201301938 http://doi.org/10.1002/adma.201301938 .

Liu, L. J.; Liu, W.; Ji, G.; Wu, Z. Y.; Xu, B.; Qian, J.; Tian, W. J . NIR emission nanoparticles based on FRET composed of AIE luminogens and NIR dyes for two-photon fluorescence imaging . Chinese J. Polym. Sci. , 2019 . 37 401 - 408 . DOI: 10.1007/s10118-019-2206-3 http://doi.org/10.1007/s10118-019-2206-3 .

Zhang, X.; Zhang, X.; Wang, S.; Liu, M.; Tao, L.; Wei, Y . Surfactant modification of aggregation-induced emission material as biocompatible nanoparticles: Facile preparation and cell imaging . Nanoscale , 2013 . 5 147 - 150 . DOI: 10.1039/C2NR32698A http://doi.org/10.1039/C2NR32698A .

Wu, X.; Sun, S.; Wang, Y.; Zhu, J.; Jiang, K.; Leng, Y.; Shu, Q.; Lin, H . A fluorescent carbon-dots-based mitochondria-targetable nanoprobe for peroxynitrite sensing in living cells . Biosens. Bioelectron. , 2017 . 90 501 - 507 . DOI: 10.1016/j.bios.2016.10.060 http://doi.org/10.1016/j.bios.2016.10.060 .

Tang, L.; Wu, T.; Tang, Z. W.; Xiao, J. Y.; Zhuo, R. X.; Shi, B.; Liu, C. J . Water-soluble photoluminescent fullerene capped mesoporous silica for pH-responsive drug delivery and bioimaging . Nanotechnology , 2016 . 27 315104 DOI: 10.1088/0957-4484/27/31/315104 http://doi.org/10.1088/0957-4484/27/31/315104 .

Larson, D. R.; Zipfel, W. R.; Williams, R. M.; Clark, S. W.; Bruchez, M. P.; Wise, F. W.; Webb, W. W . Water-soluble quantum dots for multiphoton fluorescence imaging in vivo . Science , 2003 . 300 1434 - 1436 . DOI: 10.1126/science.1083780 http://doi.org/10.1126/science.1083780 .

Michalet, X.; Pinaud, F. F.; Bentolila, L. A.; Tsay, J. M.; Doose, S.; Li, J. J.; Sundaresan, G.; Wu, A. M.; Gambhir, S. S.; Weiss, S . Quantum dots for live cells, in vivo imaging, and diagnostics . Science , 2005 . 307 538 DOI: 10.1126/science.1104274 http://doi.org/10.1126/science.1104274 .

Li, K.; Liu, B . Polymer-encapsulated organic nanoparticles for fluorescence and photoacoustic imaging . Chem. Soc. Rev. , 2014 . 43 6570 - 6597 . DOI: 10.1039/C4CS00014E http://doi.org/10.1039/C4CS00014E .

Feng, G.; Mao, D.; Liu, J.; Goh, C. C.; Ng, L. G.; Kong, D.; Tang, B. Z.; Liu, B . Polymeric nanorods with aggregation-induced emission characteristics for enhanced cancer targeting and imaging . Nanoscale , 2018 . 10 5869 - 5874 . DOI: 10.1039/C7NR09196F http://doi.org/10.1039/C7NR09196F .

Zhang, X.; Wang, K.; Liu, M.; Zhang, X.; Tao, L.; Chen, Y.; Wei, Y . Polymeric AIE-based nanoprobes for biomedical applications: Recent advances and perspectives . Nanoscale , 2015 . 7 11486 - 11508 . DOI: 10.1039/C5NR01444A http://doi.org/10.1039/C5NR01444A .

Zhan, R.; Pan, Y.; Manghnani, P. N.; Liu, B . AIE polymers: Synthesis, properties, and biological applications . Macromol. Biosci. , 2017 . 17 1600433 DOI: 10.1002/mabi.v17.5 http://doi.org/10.1002/mabi.v17.5 .

Ma, C.; Xie, G.; Zhang, X.; Yang, L.; Li, Y.; Liu, H.; Wang, K.; Wei, Y . Biocompatible fluorescent polymers from PEGylation of an aggregation-induced emission dye . Dyes Pigments , 2017 . 139 672 - 680 . DOI: 10.1016/j.dyepig.2016.12.070 http://doi.org/10.1016/j.dyepig.2016.12.070 .

Zhou, D.; Zhang, G.; Yu, Q.; Gan, Z . Folic acid modified polymeric micelles for intravesical instilled chemotherapy . Chinese J. Polym. Sci. , 2018 . 36 479 - 487 . DOI: 10.1007/s10118-018-2009-y http://doi.org/10.1007/s10118-018-2009-y .

He, J.; Chen, H.; Guo, Y.; Wang, L.; Zhu, L.; Karahan, H. E.; Chen, Y . Polycondensation of a perylene bisimide derivative and L-malic acid as water-soluble conjugates for fluorescent labeling of live mammalian cells . Polymers , 2018 . 10 559 DOI: 10.3390/polym10050559 http://doi.org/10.3390/polym10050559 .

Wang, K.; Zhang, X.; Zhang, X.; Ma, C.; Li, Z.; Huang, Z.; Zhang, Q.; Wei, Y . Preparation of emissive glucose-containing polymer nanoparticles and their cell imaging applications . Polym. Chem. , 2015 . 6 4455 - 4461 . DOI: 10.1039/C5PY00378D http://doi.org/10.1039/C5PY00378D .

Huang, Z.; Zhang, X.; Zhang, X.; Wang, S.; Yang, B.; Wang, K.; Yuan, J.; Tao, L.; Wei, Y . Synthesis of amphiphilic fluorescent copolymers with smart pH sensitivity via RAFT polymerization and their application in cell imaging . Polym. Bull. , 2017 . 74 4525 - 4536 . DOI: 10.1007/s00289-017-1969-3 http://doi.org/10.1007/s00289-017-1969-3 .

Hua, Z.; Wilks, T. R.; Keogh, R.; Herwig, G.; Stavros, V. G.; O’Reilly, R. K . Entrapment and rigidification of adenine by a photo-cross-linked thymine network leads to fluorescent polymer nanoparticles . Chem. Mater. , 2018 . 30 1408 - 1416 . DOI: 10.1021/acs.chemmater.7b05206 http://doi.org/10.1021/acs.chemmater.7b05206 .

Yang, H. M.; Park, C. W.; Park, S.; Kim, J. D . Cross-linked magnetic nanoparticles with a biocompatible amide bond for cancer-targeted dual optical/magnetic resonance imaging . Colloids Surf., B , 2018 . 161 183 - 191 . DOI: 10.1016/j.colsurfb.2017.10.049 http://doi.org/10.1016/j.colsurfb.2017.10.049 .

Zhang, X.; Zhang, X.; Yang, B.; Liu, M.; Liu, W.; Chen, Y.; Wei, Y . Fabrication of aggregation induced emission dye-based fluorescent organic nanoparticles via emulsion polymerization and their cell imaging applications . Polym. Chem. , 2014 . 5 399 - 404 . DOI: 10.1039/C3PY00984J http://doi.org/10.1039/C3PY00984J .

Shen, X.; Shi, Y.; Peng, B.; Li, K.; Xiang, J.; Zhang, G.; Liu, Z.; Chen, Y.; Zhang, D . Fluorescent polymeric micelles with tetraphenylethylene moieties and their application for the selective detection of glucose . Macromol. Biosci. , 2012 . 12 1583 - 1590 . DOI: 10.1002/mabi.v12.11 http://doi.org/10.1002/mabi.v12.11 .

Lim, C. K.; Kim, S.; Kwon, I. C.; Ahn, C. H.; Park, S. Y . Dye-condensed biopolymeric hybrids: Chromophoric aggregation and self-assembly toward fluorescent bionanoparticles for near infrared bioimaging . Chem. Mater. , 2009 . 21 5819 - 5825 . DOI: 10.1021/cm902379x http://doi.org/10.1021/cm902379x .

Lu, H.; Su, F.; Mei, Q.; Zhou, X.; Tian, Y.; Tian, W.; Johnson, R. H.; Meldrum, D. R . A series of poly[ N -(2-hydroxypropyl)methacrylamide] copolymers with anthracene-derived fluorophores showing aggregation-induced emission properties for bioimaging . J. Polym. Sci., Part A: Polym. Chem. , 2012 . 50 890 - 899 . DOI: 10.1002/pola.v50.5 http://doi.org/10.1002/pola.v50.5 .

Zhang, X.; Zhang, X.; Yang, B.; Hui, J.; Liu, M.; Chi, Z.; Liu, S.; Xu, J.; Wei, Y . Facile preparation and cell imaging applications of fluorescent organic nanoparticles that combine AIE dye and ring-opening polymerization . Polym. Chem. , 2014 . 5 318 - 322 . DOI: 10.1039/C3PY01143G http://doi.org/10.1039/C3PY01143G .

Zhang, X.; Zhang, X.; Yang, B.; Hui, J.; Liu, M.; Liu, W.; Chen, Y.; Wei, Y . PEGylation and cell imaging applications of AIE based fluorescent organic nanoparticles via ring-opening reaction . Polym. Chem. , 2014 . 5 689 - 693 . DOI: 10.1039/C3PY01272G http://doi.org/10.1039/C3PY01272G .

Chithrani, B. D.; Chan, W. C. W . Elucidating the mechanism of cellular uptake and removal of protein-coated gold nanoparticles of different sizes and shapes . Nano Lett. , 2007 . 7 1542 - 1550 . DOI: 10.1021/nl070363y http://doi.org/10.1021/nl070363y .

Barua, S.; Yoo, J. W.; Kolhar, P.; Wakankar, A.; Gokarn, Y. R.; Mitragotri, S . Particle shape enhances specificity of antibody-displaying nanoparticles . Proc. Nat. Acad. Sci. , 2013 . 110 3270 DOI: 10.1073/pnas.1216893110 http://doi.org/10.1073/pnas.1216893110 .

Salata, O. V . Applications of nanoparticles in biology and medicine . J. Nanobiotechnol. , 2004 . 2 3 DOI: 10.1186/1477-3155-2-3 http://doi.org/10.1186/1477-3155-2-3 .

Albanese, A.; Tang, P. S.; Chan, W. C. W . The effect of nanoparticle size, shape, and surface chemistry on biological systems . Annu. Rev. Biomed. Eng. , 2012 . 14 1 - 16 . DOI: 10.1146/annurev-bioeng-071811-150124 http://doi.org/10.1146/annurev-bioeng-071811-150124 .

Ding, L.; Zhou, S.; Li, D.; Wu, C.; Xing, Y.; Song, B . A facile method to incorporate tetraphenylethylene into polymeric amphiphiles: High emissive nanoparticles for cell-imaging . Dyes Pigments , 2019 . 160 711 - 716 . DOI: 10.1016/j.dyepig.2018.08.063 http://doi.org/10.1016/j.dyepig.2018.08.063 .

Gauthier, M. A.; Gibson, M. I.; Klok, H. A . Synthesis of functional polymers by post-polymerization modification . Angew. Chem. Int. Ed. , 2009 . 48 48 - 58 . DOI: 10.1002/anie.200801951 http://doi.org/10.1002/anie.200801951 .

Günay, K. A.; Theato, P.; Klok, H. A . Standing on the shoulders of Hermann Staudinger: Post-polymerization modification from past to present . J. Polym. Sci., Part A: Polym. Chem. , 2013 . 51 1 - 28 . DOI: 10.1002/pola.26333 http://doi.org/10.1002/pola.26333 .

Hong, Y.; Lam, J. W. Y.; Tang, B. Z . Aggregation-induced emission . Chem. Soc. Rev. , 2011 . 40 5361 - 5388 . DOI: 10.1039/c1cs15113d http://doi.org/10.1039/c1cs15113d .

Mei, J.; Leung, N. L. C.; Kwok, R. T. K.; Lam, J. W. Y.; Tang, B. Z . Aggregation-induced emission: Together we shine, united we soar! . Chem. Rev. , 2015 . 115 11718 - 11940 . DOI: 10.1021/acs.chemrev.5b00263 http://doi.org/10.1021/acs.chemrev.5b00263 .

Zhao, Y.; Wu, Y.; Yan, G.; Zhang, K . Aggregation-induced emission block copolymers based on ring-opening metathesis polymerization . RSC Adv. , 2014 . 4 51194 - 51200 . DOI: 10.1039/C4RA08191A http://doi.org/10.1039/C4RA08191A .

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Controllable Emission via Tuning the Size of Fluorescent Nano-probes Formed by Polymeric Amphiphiles

DOI：10.1007/s10118-019-2256-6

摘要

Abstract

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